supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

ci2654 scheme

Acta Cryst. (2008). E64, o1759    [ doi:10.1107/S1600536808025828 ]

4-Chloro-N'-(2-hydroxy-1-naphthylidene)benzohydrazide

D.-S. Yang

Abstract top

The molecule of the title compound, C18H13ClN2O2, displays a trans configuration with respect to the C=N double bond. The dihedral angle between the benzene and naphthyl ring systems is 6.0 (2)°. An O-H...N hydrogen bond is observed in the molecular structure. In the crystal structure, molecules are linked through intermolecular N-H...O hydrogen bonds and [pi]-[pi] stacking interactions [centroid-centroid distance = 3.603 (2) Å], forming chains running along the b axis.

Comment top

Schiff base compounds have been of great interest for a long time. These compounds play an important role in the development of coordination chemistry (Musie et al., 2001; Bernardo et al., 1996; Paul et al., 2002). Recently, we have reported crystal structures of a few Schiff base compounds (Yang, 2006a,b,c,d,e, 2007a,b,c; Yang & Guo, 2006). As a further investigation of this work, the crystal structure of the title compound is reported here.

The molecule of the title compound displays a trans configuration with respect to the C═N double bond (Fig. 1). The dihedral angle between the benzene and naphthyl rings is 6.0 (2)°. All the bond lengths are within normal ranges (Allen et al., 1987). The C11═N1 bond length of 1.275 (3) Å conforms to the value for a double bond. The bond length of 1.353 (3) Å between atoms C12 and N2 is intermediate between an N—N single bond and an N═N double bond, because of conjugation effects in the molecule. An intramolecular O—H···N hydrogen bond is observed.

In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains running along the b axis (Fig. 2). The chain is strengthened by π–π interactions between C1–C5/C10 and C5–C10 benzene rings (centroid–centroid distance is 3.603 (2) Å).

Related literature top

For related structures, see: Yang (2006a,b,c,d,e, 2007a,b,c); Yang & Guo (2006). For related literature, see: Bernardo et al. (1996); Musie et al. (2001); Paul et al. (2002). For bond-length data, see: Allen et al. (1987).

Experimental top

2-Hydroxy-1-naphthylaldehyde (0.1 mmol, 17.2 mg) and 4-chlorobenzohydrazide (0.1 mmol, 17.0 mg) were dissolved in methanol (10 ml). The mixture was stirred at room temperature to give a clear colourless solution. Single crystals of the title compound were obtained by gradual evaporation of the solvent over a period of 8 d at room temperature.

Refinement top

Atom H2 was located in a difference Fourier map and refined isotropically, with the N—H distance restrained to 0.90 (1) Å. Other H atoms were placed in idealized positions and constrained to ride on their parent atoms, with O—H = 0.82 Å, C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Crystal packing packing of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.
4-Chloro-N'-(2-hydroxy-1-naphthylidene)benzohydrazide top
Crystal data top
C18H13ClN2O2F000 = 336
Mr = 324.75Dx = 1.442 Mg m−3
Monoclinic, PcMo Kα radiation
λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 2145 reflections
a = 6.200 (3) Åθ = 2.8–29.3º
b = 4.788 (2) ŵ = 0.27 mm−1
c = 25.320 (11) ÅT = 298 (2) K
β = 95.844 (7)ºBlock, colourless
V = 747.8 (6) Å30.23 × 0.21 × 0.20 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer		2197 independent reflections
Radiation source: fine-focus sealed tube2039 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.017
T = 298(2) Kθmax = 27.0º
ω scansθmin = 3.2º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −5→7
Tmin = 0.941, Tmax = 0.949k = −6→6
4001 measured reflectionsl = −31→26
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of
independent and constrained refinement
R[F2 > 2σ(F2)] = 0.032  w = 1/[σ2(Fo2) + (0.0403P)2 + 0.1026P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.080(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.12 e Å−3
2197 reflectionsΔρmin = −0.19 e Å−3
212 parametersExtinction correction: none
3 restraintsAbsolute structure: Flack (1983), with 596 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.03 (7)
Secondary atom site location: difference Fourier map
Crystal data top
C18H13ClN2O2V = 747.8 (6) Å3
Mr = 324.75Z = 2
Monoclinic, PcMo Kα
a = 6.200 (3) ŵ = 0.27 mm−1
b = 4.788 (2) ÅT = 298 (2) K
c = 25.320 (11) Å0.23 × 0.21 × 0.20 mm
β = 95.844 (7)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		2197 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2039 reflections with I > 2σ(I)
Tmin = 0.941, Tmax = 0.949Rint = 0.017
4001 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.080Δρmax = 0.12 e Å−3
S = 1.05Δρmin = −0.19 e Å−3
2197 reflectionsAbsolute structure: Flack (1983), with 596 Friedel pairs
212 parametersFlack parameter: 0.03 (7)
3 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl11.44733 (12)0.28331 (19)0.25960 (4)0.0780 (3)
N10.3640 (3)0.4990 (4)0.05683 (7)0.0395 (4)
N20.5480 (3)0.4210 (4)0.08892 (8)0.0390 (4)
O10.0022 (3)0.7705 (3)0.04417 (7)0.0512 (4)
H10.12200.72930.05890.077*
O20.5730 (3)0.8546 (3)0.12464 (7)0.0504 (4)
C10.0931 (3)0.3955 (4)−0.01348 (9)0.0378 (5)
C2−0.0450 (3)0.6040 (4)0.00131 (9)0.0404 (5)
C3−0.2478 (4)0.6510 (5)−0.02775 (11)0.0515 (6)
H3−0.34130.7847−0.01630.062*
C4−0.3071 (4)0.5020 (5)−0.07244 (11)0.0529 (6)
H4−0.44220.5341−0.09090.063*
C5−0.1684 (4)0.2987 (5)−0.09167 (10)0.0458 (5)
C6−0.2251 (4)0.1535 (5)−0.13960 (10)0.0544 (6)
H6−0.35800.1895−0.15890.065*
C7−0.0893 (5)−0.0380 (6)−0.15817 (10)0.0587 (7)
H7−0.1289−0.1318−0.18980.070*
C80.1105 (5)−0.0923 (6)−0.12918 (10)0.0549 (6)
H80.2035−0.2233−0.14180.066*
C90.1709 (4)0.0441 (5)−0.08267 (9)0.0478 (6)
H90.30510.0049−0.06430.057*
C100.0348 (3)0.2428 (5)−0.06184 (9)0.0384 (5)
C110.2922 (3)0.3316 (5)0.01999 (9)0.0393 (5)
H110.36730.16780.01450.047*
C120.6429 (3)0.6152 (4)0.12246 (8)0.0371 (5)
C130.8398 (3)0.5189 (4)0.15662 (8)0.0357 (4)
C140.8939 (4)0.6535 (5)0.20461 (10)0.0468 (6)
H140.80450.79410.21530.056*
C151.0795 (4)0.5809 (6)0.23675 (10)0.0532 (6)
H151.11550.67010.26910.064*
C161.2100 (4)0.3728 (5)0.21960 (9)0.0483 (6)
C171.1626 (4)0.2370 (5)0.17207 (10)0.0449 (5)
H171.25430.09910.16130.054*
C180.9751 (3)0.3101 (4)0.14053 (9)0.0407 (5)
H180.93930.21890.10840.049*
H20.576 (6)0.240 (3)0.0963 (14)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0468 (3)0.1144 (6)0.0692 (4)0.0089 (4)−0.0112 (3)0.0192 (4)
N10.0344 (9)0.0357 (9)0.0476 (10)0.0038 (7)0.0003 (8)0.0045 (7)
N20.0373 (9)0.0305 (8)0.0475 (10)0.0053 (8)−0.0031 (8)0.0022 (7)
O10.0545 (10)0.0446 (9)0.0552 (10)0.0141 (8)0.0086 (8)0.0030 (8)
O20.0490 (9)0.0290 (7)0.0715 (11)0.0077 (7)−0.0016 (8)−0.0015 (7)
C10.0326 (11)0.0347 (10)0.0460 (12)0.0008 (9)0.0040 (9)0.0108 (9)
C20.0382 (12)0.0373 (12)0.0465 (12)0.0038 (9)0.0086 (9)0.0103 (9)
C30.0400 (12)0.0496 (14)0.0662 (16)0.0121 (11)0.0114 (11)0.0140 (12)
C40.0336 (12)0.0531 (14)0.0700 (17)0.0073 (10)−0.0036 (11)0.0165 (12)
C50.0367 (12)0.0431 (12)0.0561 (14)−0.0036 (10)−0.0017 (10)0.0164 (10)
C60.0490 (14)0.0546 (15)0.0558 (15)−0.0049 (12)−0.0129 (11)0.0132 (12)
C70.0672 (17)0.0599 (16)0.0468 (15)−0.0122 (14)−0.0056 (12)0.0016 (12)
C80.0576 (14)0.0563 (15)0.0507 (15)0.0031 (12)0.0050 (11)−0.0020 (12)
C90.0427 (13)0.0486 (13)0.0512 (14)0.0048 (10)0.0008 (10)0.0022 (10)
C100.0330 (10)0.0350 (12)0.0466 (12)−0.0017 (8)0.0014 (8)0.0102 (8)
C110.0345 (11)0.0343 (10)0.0491 (12)0.0053 (8)0.0038 (9)0.0047 (9)
C120.0367 (11)0.0311 (10)0.0439 (12)0.0030 (9)0.0059 (9)0.0046 (8)
C130.0371 (11)0.0283 (10)0.0416 (11)0.0005 (8)0.0030 (8)0.0041 (8)
C140.0503 (14)0.0391 (12)0.0510 (14)0.0056 (10)0.0053 (11)−0.0025 (10)
C150.0540 (15)0.0598 (16)0.0443 (14)−0.0019 (12)−0.0028 (11)−0.0037 (11)
C160.0352 (11)0.0594 (15)0.0489 (14)−0.0019 (11)−0.0020 (10)0.0163 (11)
C170.0371 (12)0.0464 (13)0.0518 (14)0.0093 (10)0.0074 (10)0.0080 (10)
C180.0398 (12)0.0373 (11)0.0453 (12)0.0029 (9)0.0051 (9)0.0022 (9)
Geometric parameters (Å, °) top
Cl1—C161.752 (2)C6—H60.93
N1—C111.275 (3)C7—C81.398 (4)
N1—N21.383 (2)C7—H70.93
N2—C121.353 (3)C8—C91.365 (3)
N2—H20.899 (10)C8—H80.93
O1—C21.354 (3)C9—C101.410 (3)
O1—H10.82C9—H90.93
O2—C121.228 (2)C11—H110.93
C1—C21.392 (3)C12—C131.495 (3)
C1—C101.440 (3)C13—C141.386 (3)
C1—C111.457 (3)C13—C181.392 (3)
C2—C31.409 (3)C14—C151.385 (3)
C3—C41.356 (4)C14—H140.93
C3—H30.93C15—C161.381 (4)
C4—C51.418 (4)C15—H150.93
C4—H40.93C16—C171.373 (3)
C5—C61.412 (4)C17—C181.387 (3)
C5—C101.427 (3)C17—H170.93
C6—C71.361 (4)C18—H180.93
C11—N1—N2117.76 (18)C8—C9—H9119.2
C12—N2—N1117.57 (16)C10—C9—H9119.2
C12—N2—H2118 (2)C9—C10—C5117.3 (2)
N1—N2—H2121 (2)C9—C10—C1123.55 (19)
C2—O1—H1109.5C5—C10—C1119.1 (2)
C2—C1—C10119.01 (18)N1—C11—C1120.4 (2)
C2—C1—C11120.14 (19)N1—C11—H11119.8
C10—C1—C11120.85 (19)C1—C11—H11119.8
O1—C2—C1123.34 (19)O2—C12—N2122.48 (19)
O1—C2—C3115.7 (2)O2—C12—C13122.18 (19)
C1—C2—C3121.0 (2)N2—C12—C13115.34 (16)
C4—C3—C2120.2 (2)C14—C13—C18119.4 (2)
C4—C3—H3119.9C14—C13—C12118.30 (19)
C2—C3—H3119.9C18—C13—C12122.20 (19)
C3—C4—C5121.7 (2)C15—C14—C13120.7 (2)
C3—C4—H4119.2C15—C14—H14119.6
C5—C4—H4119.2C13—C14—H14119.6
C6—C5—C4121.8 (2)C16—C15—C14118.3 (2)
C6—C5—C10119.5 (2)C16—C15—H15120.8
C4—C5—C10118.7 (2)C14—C15—H15120.8
C7—C6—C5121.3 (2)C17—C16—C15122.5 (2)
C7—C6—H6119.3C17—C16—Cl1118.9 (2)
C5—C6—H6119.3C15—C16—Cl1118.62 (19)
C6—C7—C8119.4 (2)C16—C17—C18118.5 (2)
C6—C7—H7120.3C16—C17—H17120.7
C8—C7—H7120.3C18—C17—H17120.7
C9—C8—C7121.0 (3)C17—C18—C13120.5 (2)
C9—C8—H8119.5C17—C18—H18119.8
C7—C8—H8119.5C13—C18—H18119.8
C8—C9—C10121.6 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.872.584 (2)145
N2—H2···O2i0.90 (1)1.98 (1)2.858 (3)165 (4)
Symmetry codes: (i) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.872.584 (2)145
N2—H2···O2i0.90 (1)1.98 (1)2.858 (3)165 (4)
Symmetry codes: (i) x, y−1, z.
Acknowledgements top

The author acknowledges Key Laboratory Construction Support from the Education Office of Shanxi Province (Project No. 05JS43).

references
References top

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Bernardo, K., Leppard, S., Robert, A., Commenges, G., Dahan, F. & Meunier, B. (1996). Inorg. Chem. 35, 387–396.

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Musie, G. T., Wei, M., Subramaniam, B. & Busch, D. H. (2001). Inorg. Chem. 40, 3336–3341.

Paul, S., Barik, A. K., Peng, S. M. & Kar, S. K. (2002). Inorg. Chem. 41, 5803–5809.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Yang, D.-S. (2006a). Acta Cryst. E62, o1395–o1396.

Yang, D.-S. (2006b). Acta Cryst. E62, o1591–o1592.

Yang, D.-S. (2006c). Acta Cryst. E62, o2365–o2366.

Yang, D.-S. (2006d). Acta Cryst. E62, o3755–o3756.

Yang, D.-S. (2006e). Acta Cryst. E62, o3792–o3793.

Yang, D.-S. (2007a). J. Chem. Crystallogr. 37, 343–348.

Yang, D.-S. (2007b). Acta Cryst. E63, o3738.

Yang, D.-S. (2007c). Acta Cryst. E63, o3739.

Yang, D.-S. & Guo, J.-B. (2006). Acta Cryst. E62, o4414–o4415.